Pushing Back on a Strategy

A black and white photo of a gentleman riding a pig. The man is dressed like a train conductor. The pig is a large boar, seems happy enough. Reins, a bridle, and a saddle are being used.

Let’s say you’ve been told to make a change and you’ve taken it to the team, and after everyone’s calmed down and thought about it, you are personally convinced it’s the wrong move. You now have a conflict, potentially serious, with the organization’s direction. What then? Are you going to push back, or let it slide?

No matter what, start by recognizing and processing your emotions. You can’t be going to leadership with shouting instead of data, they’ve got plenty of that between themselves and don’t need more from you. After you’re able to talk about this without raising your voice, evaluate the scope of the conflict. Is this really important? Imagine that you’re going to ask the executive staff to listen to your concerns for half an hour; that’s not going to be cheap or easy, so don’t waste the effort for unimportant stuff.

Prepare your thoughts and give it your best shot. Propose what should be done, bring supporting data, present clearly. That advice assumes there is a good alternative path; if your concern is that the alternative is dumb and you think the organization should stay on its prior path, just be cautious that executive staff may already be convinced that the old path is no good. Pre-work involves finding out from your boss and/or skip-level what’s accepted ground truth with your audience. This is also a great way to get your boss and skip-level to review your presentation; which is very good practice for all involved.

If you push back and it doesn’t work, you are left with disagree and commit. In its ideal form, this strategy means that you do your best to make the project work. It’s not disagree-and-participate after all, it’s commit in the chicken and pig sense. It may help to ask the people who wanted this change to explain again why it’s a good idea. Since it’s already committed, you’re not there to re-fight past battles, you’re there to learn. Even if that session leaves you unconvinced, you should take the project as a way to focus on the fundamentals of product management. Particularly for a new product manager coming from a more technical subject matter expert role, you might have only been working on projects where you have strong personal ties to the use cases and personas. Maybe this organizational pivot represents a new set of problems to solve and you can focus on using your tools to understand those problems and drive solutions. I am a better product manager from working on a wide variety of problems instead of staying on one.

Caution: Work to Rule is a bad look in enterprise environments — whether you think this plan is right or not, if you commit you need to get it done well and efficiently. Maybe your model of the situation was wrong and leadership was right and this solution you’re building will really work. Or maybe you were right, but a sincere effort to put the square peg into the round hole helps leadership see that this path isn’t feasible. Sometimes the king dies, or maybe the horse sings. Don’t count on it, but a thin ray of hope might help your darkest days go by a little easier.

Why not just quit? It’s not always possible and very rarely wise to ragequit your job. Dependents need to eat and mortgages need to be paid after all. That said, a consistent pattern of decisions that you don’t agree with is a reliable sign that you and the organization aren’t aligned. If you’re in this situation, the first place to look is your boss. They are your support through the process, your visibility into leadership’s current thoughts, and your shield if a given outcome goes wrong. If it’s possible to salvage your alignment with the organization’s strategy, they’re the ones to help you get there. Your engineering team is not the right support; they’re just looking for clarity, and don’t need to be whiplashed through your process. You can certainly rely on your first team for help, but the person you report to is the critical path. You need to have a reasonably open conversation which looks like this:

  • I have concerns that we’re heading in the wrong direction. Can you help me understand what goal we’re aiming for with these changes?
  • If I’m wrong, then the right thing to do is to succeed with these changes. Can you help me execute to this plan to the best of my abilities?
  • If I’m right, then executing this plan won’t end well. Can you support that I was doing what I was asked to the best of my abilities?
  • Do not present your boss with an ultimatum. The purpose of this conversation is to find a way to stay committed and engaged. Whether it’s correct or not, the organization’s strategy is bigger than a middle manager, and the answer to “I won’t do this” is almost certainly “well, bye then.” If you’re still in an ultimatum-throwing mood after two weeks of processing time, you might need to think about exiting the organization on your terms.

Note that not every boss is capable of providing all that support. It’s possible to handle this sort of disagree-and-commit on your own of course, and you can just decide to process all this on your own without ever asking for their help. If you have to or chose to take this path, be aware of its costs. Particularly if it’s your first time going through disagree-and-commit, and particularly if it’s a tightly bonded organization, you may go through a mild form of the Kübler-Ross stages of grief. This is mourning the vision that you had of your organization and your working relationships within it. If you’ve heard seasoned managers half-joke about being dead inside, this is why: we’ve gone through this process many times.

If you can’t proceed sincerely, actually commit to or deliver on the project, then it’s going to be harder to avoid a bad outcome. It’s best to not accept it at all. Because you’ve publicly expected it to fail, its eventual failure can reflect poorly on you. You’re less likely to end up holding a bag if you can point to sincere efforts to succeed and your boss backs you up. Project refusal is not feasible in some organizations of course, and you may have no choice. Your best option in that case is to rely on your boss’s support, potentially while preparing your exit.

Preparing your exit will be a longer article than this, but it certainly starts with a resume refresh, and requires thinking about your compensation.

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